ISSN:
0170-2041
Keywords:
Soladunalinidine
;
5α-Tomatidan-3β-amine
;
5α-Solasodan-3α-amine and -3β-amine
;
5α-Spirosolan-3-amines
;
Solanum steroid alkaloids
;
Steroids
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The steroid alkaloid soladunalinidine [5α-tomatidan-3β-amine, (25S)-5α,22βN-spirosolan-3β-amine, 2], isolated from Solanum dunalianum, is synthesized from tomatidine (5α-tomatidan-3β-ol, 1) via 5α-tomatidan-3-one (4) and its oxime 5 which is reduced to 2 as well as to its ring-E-opened (22S) and (22R) dihydro products 6 and 9, the N(22,26)-chloro-N(3)-(2-hydroxy-benzylidene) derivatives 8 and 11 of which are recyclized to N(3)-(2-hydroxybenzylidene)soladunalinidine (3). The 5α-spirosolan-3-amines stereoisomeric at C-22 and C-25, 5α-solasodan-3α-amine (13) and -3β-amine (15), are obtained in an analogous sequence of reactions from soladulcidine (5α-solasodan-3β-ol, 12).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199019900199
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